EP0593520A1 - Compositions oculaires contenant des stero des et leur utilisation pour le traitement du glaucome - Google Patents
Compositions oculaires contenant des stero des et leur utilisation pour le traitement du glaucomeInfo
- Publication number
- EP0593520A1 EP0593520A1 EP92912769A EP92912769A EP0593520A1 EP 0593520 A1 EP0593520 A1 EP 0593520A1 EP 92912769 A EP92912769 A EP 92912769A EP 92912769 A EP92912769 A EP 92912769A EP 0593520 A1 EP0593520 A1 EP 0593520A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- general formula
- pharmaceutical composition
- composition according
- represents hydrogen
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Definitions
- the invention relates to the field of therapeutic chemistry and particularly to the field of pharmacotechnology.
- compositions for ocular application characterized in that they contain, as active principle, at least one compound of steroid structure chosen from the group consisting of:
- R 1 represents a hydroxy, alkoxy, acyloxy radical
- R 2 represents hydrogen or a lower alkyl radical
- R and R ' together form a keto group, hydroxyimino, alkoxy imino or acyloxy imino
- R H
- R ' is a hydroxy, alkoxy or acyloxy group
- R-. represents a lower alkyl radical having from 1 to 3 carbon atoms
- R 2 represents a hydrogen atom or an alkyl radical having from 1 to 6 carbon atoms, in a linear or branched chain
- R 7 represents a lower alkyl radical, identical or different from
- R 2 having from 1 to 6 carbon atoms, in a linear or branched chain and R, is defined as above
- R 1 represents a hydroxy, alkoxy, acyloxy or alkyl radical having from 1 to 4 atoms
- R 2 represents hydrogen or a lower alkyl radical in a straight or branched chain having from 1 to 4 carbon atoms
- Z represents hydrogen, an alkyl radical or an acyl radical and the dotted line a possible carbon-carbon double bond.
- R 1 represents a hydroxy, alkoxy, acyloxy or alkyl radical having from 1 to 4 carbon atoms
- R 2 represents hydrogen or a lower alkyl radical, in a straight or branched chain, having from 1 to 4 carbon atoms and the dotted line symbolizes a possible carbon-carbon double bond.
- X represents a halogen atom
- R 1 and R 2 are defined as above
- R 1 represents hydrogen, lower alkyl or an acyl radical derived from an organic carboxylic acid having from 1 to 10 carbon atoms
- R ' represents hydrogen or lower alkynyl
- R represents methyl or ethyl
- R 5 represents two hydrogens or the group
- R represents a lower alkyl or lower cycloalkyl radical
- R 1 and E 3 are defined as above
- R 1 is defined as above
- R 1 represents a free, etherified or esterified hydroxyl or a lower alkyl radical
- R 3 represents hydrogen or a lower alkyl radical having from 1 to 4 carbon atoms
- R represents hydrogen or an acyl radical derived from an organic carboxylic acid having from 1 to 10 carbon atoms.
- R represents hydrogen or an acyl radical derived from an organic carboxylic acid having from 1 to 10 carbon atoms.
- R 1 represents hydrogen, a lower alkyl radical, a methoxy alkyl, an acyl derived from an organic carboxylic acid or alkyl carbonic acid
- R represents hydrogen or an optionally substituted lower alkyl radical
- R 3 represents hydrogen, a halogen or a lower alkyl and the wavy line symbolizes an ⁇ or ⁇ orientation in association or in mixture with an excipient or an inert, pharmaceutically acceptable vehicle, intended for use by the ocular route.
- compositions are, according to the invention, preferably presented in solid form with extemporaneous dissolution, semi-solid or liquid, the compounds of formula I, of formula II, of formula III, of formula IV, of formula V, of formula VI, of formula VII, of formula IX, of formula X, of formula XI or of formula XII being in the form of suspension or dissolved in solution, distributed in vials, tubes or single-dose systems.
- R 7 represents a hydrogen atom, an acyl radical having from 1 to 8 carbon atoms
- R 3 is a methyl or propyl radical
- R 7 represents a hydrogen atom, an alkyl radical having from 1 to 8 carbon atoms, a tetrahydropyranyl-2 radical or an acyl radical derived from an aliphatic carboxylic acid, saturated or unsaturated, having from 1 to 10 atoms carbon, optionally substituted by an aryl or cycloalkyl radical
- R 4 represents a hydrogen atom, a lower alkyl radical, a methoxymethyl radical, a tetrahydropyranyl-2 radical or an acyl radical of an organic carboxylic acid having from 1 to 10 carbon atoms
- R represents a lower alkyl radical, identical or different from
- R 'and R " having 1 to 3 carbon atoms in a linear or branched chain
- R 1 is an alkyl radical, a hydroxy, an alkoxy, an acyloxy
- R 1 represents hydrogen, an optionally substituted alkyl radical or an acyl radical derived from an organic carboxylic acid or a carbonic alkyl acid having from 1 to 8 carbon atoms and R 3 is defined as previously b) 3-oxo 17 ⁇ -alc ⁇ yl androsta 4-ene of general formula Xllb
- R 1 represents hydrogen or an acyl radical defined as above
- R is a lower alkyl radical optionally substituted by a halogen or an acyl
- R 3 is hydrogen or lower alkyl
- the preparations thus obtained are added, if necessary, with mineral salts or organic derivatives to achieve isotonia with lacrimal secretions, preservatives or stabilizers and / or antioxidants.
- antioxidants mention will be made more particularly of chelating agents such as ethylene diaminotetraacetic acid and its salts.
- chelating agents such as ethylene diaminotetraacetic acid and its salts.
- antioxidants mention may be made of ascorbic acid, alkali metal metabisulfites, alkali metal hypophosphites, sodium salicylate, sodium gentisate or isopropyl gallate.
- a lower alkyl radical has from 1 to 6 carbon atoms such as a methyl, ethyl, isopropyl, terbutyl, isobutyl, n-pentyl, neopentyl or nhexyl radical.
- a halogen is a fluorine or chlorine atom.
- An acyl residue of organic carboxylic acid contains from 1 to 10 atoms in the carbon part such as for example an acetyl, a propionyl, a hexanoyl, a benzoyl, a dichoroacetyl, a vanilloyl, an isovanilloyl, a trimethoxy benzoyl, a naphthoyl ( ⁇ or ⁇ ), a furoyl, a nicotinoyl or a thenoyle.
- An alkyl residue of an alkyl carbonic acid contains from 1 to 8 carbon atoms in the alkyl chain, such as for example a cycloalkylmethyl carbonic acid or a cycloalkylpropyl carbonic radical.
- compositions according to the invention are intended for the treatment of intraocular hypertonia and glaucomatous disease. They contain from 0.05 to 1% of steroid active ingredient. They are carried out by dissolving or suspending an active principle in an appropriate aqueous solvent. We know that there are three types of glaucoma:
- the clinical signs of these conditions are those of optic neuropathy with:
- Intraocular pressure (IOP) greater than 15 mmHg + 2.5 mmHg is observed in the majority of cases.
- bronchial asthma bronchial asthma
- cardiovascular insufficiency etc ...
- iridocyclitis para-sympathomimetic antiglaucomatous drugs
- undesirable effects corneo-conjunctival reactions, iris mydriasis or miosis, dry eyes, changes in the visual field, cardiovascular effects, general respiratory effects, dermatology, etc.
- compositions according to the invention aim to improve this situation. They are at least equally effective, but above all their tolerance and safety at the doses intended are significantly better. In addition, they are aimed equally at open-angle glaucomas and glaucoma by closing the angle and present practically none of the undesirable effects and contraindications mentioned above.
- TZU LUNG CHIANG Prostaglandins 4, 3 (1973) 415
- progesterone inhibits the hypertensive response of the eye to the intravenous infusion of PGA 2 .
- the doses of progesterone administered were considerable (25 mg / kg).
- the same author (Europ. J. of Pharmacology 22 (1973) 304) confirmed that progesterone antagonizes the increase in intraocular pressure.
- progesterone appears to result from a synergy with the effect of epinephrine or ephedrine, administered locally.
- PGE administered as a venous infusion completely inhibits the increase in the level of protein production in the aqueous humor.
- the useful dosage ranges from 1 to 5 drops per day in each eye of a solution or suspension containing from 0.05 to 1% of an active principle of general formulas I to XII.
- the solutions or suspensions contain from 0.1 to 0.5% of active principle of general formulas I to XII.
- glaucoma is provoked one month before the tests by injection into the posterior chamber of an eye, of a proteolytic enzyme, alpha-chymotrypsin. This causes lysis of the lens zonule, dislocation of the lens in the posterior chamber and hypertension by mechanical obstruction of the iridocorneal angle.
- the compounds according to the invention at a concentration of 0.1 to 0.5%, cause a rapid, significant and concentration-related decrease in intraocular pressure.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims
Applications Claiming Priority (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9107412 | 1991-06-18 | ||
FR9107412 | 1991-06-18 | ||
FR9109017 | 1991-07-17 | ||
FR9109015A FR2679137B1 (fr) | 1991-07-17 | 1991-07-17 | Nouvelles compositions pharmaceutiques a base d'un derive pregnenique et leur procede de preparation. |
FR9109017A FR2679139B1 (fr) | 1991-07-17 | 1991-07-17 | Nouvelles compositions pharmaceutiques destinees a l'application oculaire renfermant un derive androstenique et leur procede de preparation. |
FR9109016A FR2679138B1 (fr) | 1991-07-17 | 1991-07-17 | Compositions pharmaceutiques anti-glaucomateuses et leur procede d'obtention. |
FR9109015 | 1991-07-17 | ||
FR9109016 | 1991-07-17 | ||
FR9110160A FR2680108B1 (fr) | 1991-08-09 | 1991-08-09 | Nouvelles compositions pharmaceutiques a base de sterouides 6-hydroxymethyles et leur procede d'obtention. |
FR9110160 | 1991-08-09 | ||
PCT/FR1992/000549 WO1992022300A1 (fr) | 1991-06-18 | 1992-06-18 | Compositions oculaires contenant des steroïdes et leur utilisation pour le traitement du glaucome |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0593520A1 true EP0593520A1 (fr) | 1994-04-27 |
EP0593520B1 EP0593520B1 (fr) | 1999-09-29 |
Family
ID=27515565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92912769A Expired - Lifetime EP0593520B1 (fr) | 1991-06-18 | 1992-06-18 | Compositions oculaires contenant des steroides et leur utilisation pour le traitement du glaucome |
Country Status (11)
Country | Link |
---|---|
US (1) | US5506220A (fr) |
EP (1) | EP0593520B1 (fr) |
JP (1) | JP3328729B2 (fr) |
KR (1) | KR100249555B1 (fr) |
AT (1) | ATE185071T1 (fr) |
CA (1) | CA2111699A1 (fr) |
DE (1) | DE69230069T2 (fr) |
DK (1) | DK0593520T3 (fr) |
ES (1) | ES2139602T3 (fr) |
GR (1) | GR3031967T3 (fr) |
WO (1) | WO1992022300A1 (fr) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2292239A3 (fr) * | 2003-04-18 | 2011-03-30 | Advanced Medicine Research Institute | Remèdes à des affections, à usage ophtalmique |
WO2004093882A1 (fr) * | 2003-04-18 | 2004-11-04 | Advanced Medicine Research Institute | Remedes a appliquer sur l'oeil pour soigner differentes maladies |
JP5544458B2 (ja) * | 2005-07-12 | 2014-07-09 | アンピオ ファーマシューティカルズ,インコーポレイテッド | 疾病を治療するための医薬製品の製造においてトリロスタンiiiを使用する方法及びトリロスタンiiiを含む医薬製品 |
PT2554172E (pt) | 2009-06-22 | 2014-11-07 | Ampio Pharmaceuticals Inc | Método para o tratamento de doenças |
BRPI1010086A2 (pt) * | 2009-06-22 | 2018-02-06 | Dmi Acquisition Corp | método e produtos para tratamento de doenças |
CN102134265B (zh) * | 2009-12-29 | 2013-04-03 | 黄云生 | 一种合成6-甲基-17α-乙酰氧基-19-去甲孕甾-4,6-二烯-3,20-二酮的方法 |
HUE031390T2 (en) * | 2011-05-20 | 2017-07-28 | Inserm - Inst Nat De La Sante Et De La Rech Medicale | CB1 receptor antagonists |
MX349703B (es) | 2012-11-28 | 2017-08-08 | Inst Nat Sante Rech Med | Derivados de pregnenolona. |
EA201500752A1 (ru) | 2012-12-19 | 2016-05-31 | Ампио Фармасьютикалс, Инк. | Способ лечения заболеваний |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1515284A (en) * | 1974-05-21 | 1978-06-21 | Gastaud J | Pharmaceutical compositions containing progestogens derived from the 17-alpha-hydroxy-19-nor-progesterone series |
US4383992A (en) * | 1982-02-08 | 1983-05-17 | Lipari John M | Water-soluble steroid compounds |
US4617299A (en) * | 1983-12-19 | 1986-10-14 | Knepper Paul A | Method for the prevention of ocular hypertension, treatment of glaucoma and treatment of ocular hypertension |
US4863912A (en) * | 1986-05-19 | 1989-09-05 | New York Medical College | Use of tetrahydrocortisol in glaucoma therapy |
WO1987007141A1 (fr) * | 1986-05-23 | 1987-12-03 | New England Medical Center Hospitals, Inc. | Methode de traitement du glaucome |
FR2622194B1 (fr) * | 1987-10-27 | 1990-03-23 | Theramex Laboratoire | Nouveaux derives de la 19-nor progesterone, leur procede d'obtention et les compositions pharmaceutiques en contenant |
US4876250A (en) * | 1988-10-31 | 1989-10-24 | Alcon Laboratories, Inc. | Methods for controlling ocular hypertension with angiostatic steroids |
FR2645864B1 (fr) * | 1989-04-13 | 1991-07-12 | Theramex | Nouveaux derives alcoyles en 17/21 de la 19-nor progesterone, leurs procedes d'obtention et les compositions pharmaceutiques en renfermant |
FR2679236B1 (fr) | 1991-07-18 | 1997-01-24 | Theramex | Nouveaux sterouides substitues en position 6, leurs procedes d'obtention et des compositions pharmaceutiques en renfermant. |
-
1992
- 1992-06-18 EP EP92912769A patent/EP0593520B1/fr not_active Expired - Lifetime
- 1992-06-18 WO PCT/FR1992/000549 patent/WO1992022300A1/fr active IP Right Grant
- 1992-06-18 DE DE69230069T patent/DE69230069T2/de not_active Expired - Fee Related
- 1992-06-18 AT AT92912769T patent/ATE185071T1/de not_active IP Right Cessation
- 1992-06-18 US US08/170,179 patent/US5506220A/en not_active Expired - Fee Related
- 1992-06-18 KR KR1019930703965A patent/KR100249555B1/ko not_active IP Right Cessation
- 1992-06-18 CA CA002111699A patent/CA2111699A1/fr not_active Abandoned
- 1992-06-18 JP JP50077393A patent/JP3328729B2/ja not_active Expired - Fee Related
- 1992-06-18 ES ES92912769T patent/ES2139602T3/es not_active Expired - Lifetime
- 1992-06-18 DK DK92912769T patent/DK0593520T3/da active
-
1999
- 1999-11-26 GR GR990403060T patent/GR3031967T3/el unknown
Non-Patent Citations (1)
Title |
---|
See references of WO9222300A1 * |
Also Published As
Publication number | Publication date |
---|---|
CA2111699A1 (fr) | 1992-12-23 |
US5506220A (en) | 1996-04-09 |
ATE185071T1 (de) | 1999-10-15 |
JP3328729B2 (ja) | 2002-09-30 |
DE69230069T2 (de) | 2000-05-25 |
ES2139602T3 (es) | 2000-02-16 |
GR3031967T3 (en) | 2000-03-31 |
KR940701260A (ko) | 1994-05-28 |
WO1992022300A1 (fr) | 1992-12-23 |
JPH06508362A (ja) | 1994-09-22 |
KR100249555B1 (ko) | 2000-04-01 |
DE69230069D1 (de) | 1999-11-04 |
EP0593520B1 (fr) | 1999-09-29 |
DK0593520T3 (da) | 2000-04-03 |
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